170161-34-9

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 40114-49-6 1-benzyl-3-piperidone 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide 

Relevant academic research and scientific papers

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

A Diels–Alder reaction-based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne-tethered 3-aminopyrones gives 4-substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non-canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.

SUBSTITUTED INDOLE COMPOUNDS USEFUL AS TLR INHIBITORS

Disclosed are compounds of Formula (I) N-oxides, or salts thereof, wherein G, A, R1, R5, and n are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.

Method for preparing Niraparib of PARP (poly-ADP-ribose polymerase) inhibitor

The invention discloses a method for preparing 2-(4-((3S)-3-piperidyl) phenyl)-2H-indazole-7-formamide of a compound. Benzyl protected-piperidone is generated into piperidone of 3-triflic anhydride under the action of triflic anhydride, the piperidone and nitrobenzoic acid are subjected to Suzuki reaction to obtain a coupled product, 3-(4-aminophenyl) piperidine is obtained under the action of a palladium reagent, (S)-3-(4-halogenated phenyl) piperidine is prepared with a chirality resolution reagent, the (S)-3-(4-halogenated phenyl) piperidine is condensed with 3-formyl-2-methyl nitrobenzoate to form pyrazolone ring under the action of sodium azide, and the Niraparid (with the molecular entity of 2-(4-((3S)-3-piperidyl) phenyl)-2H-indazole-7-formamide) is prepared via aminolysis.

SUBSTITUTED OXETANES AND THEIR USE AS INHIBITORS OF CATHEPSIN C

This invention relates to a compound of formula I and their use as inhibitors of Cathepsin C, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of diseases connected with dipeptidyl peptidase I activity, e.g. respiratory diseases.

SUBSTITUTED 2-AZA-BICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID (BENZYL-CYANO-METHYL)-AMIDES INHIBITORS OF CATHEPSIN C

This invention relates to 2-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid (benzyl-cyano-methyl)- amides of formula (1) and their use as inhibitors of Cathepsin C, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of diseases connected with dipeptidyl peptidase I activity, e.g. respiratory diseases.

SUBSTITUTED FUSED TRICYCLIC COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF

The present invention relates to substituted fused tricyclic compounds of formula (I) or (Ia), their tautomers, polymorphs, stereoisomers, prodrugs, solvates, co-crystals, pharmaceutically acceptable salts, pharmaceutical compositions containing them and methods of treating conditions and diseases that are mediated by JAK activity. The compounds of the present invention are useful in the treatment, prevention or suppression of diseases and disorders mediated by JAK activity. Such conditions include, but not limited to, arthritis, Alzheimer's disease, autoimmune thyroid disorders, cancer, diabetes, leukemia, T-cell prolymphocytic leukemia, lymphoma, myleoproliferation disorders, lupus, multiple myeloma, multiple sclerosis, osteoarthritis, sepsis, psoriatic arthritis, prostate cancer, T-cell autoimmune disease, inflammatory diseases, chronic and acute allograft transplant rejection, bone marrow transplant, stroke, asthma, chronic obstructive pulmonary disease, allergy, bronchitis, viral diseases, or Type I diabetes, complications from diabetes, rheumatoid arthritis, asthma, Crohn's disease, dry eye, uveitis, inflammatory bowel disease, organ transplant rejection, psoriasis and ulcerative colitis. The present disclosure also relates to process for the preparation of such compounds, and to pharmaceutical compositions containing them.

VINYLATION OF THE INDOLE 3-POSITION VIA PALLADIUM-CATALYZED CROSS-COUPLING

The palladium-catalyzed cross-coupling between 3-indoleboronic acids and vinyl triflates is an excellent method for the regioselective introduction of vinyl groups into the indole 3-position.The regioselectivity of the enolization of N-substituted 3-piperidones, as dictated by the nitrogen substituent, is far greater than previously reported.N-tosyl-3-indoleboronic acids can be easily synthesized using the mercuration-boronation methid.

Palladium catalyzed cross-coupling reaction between 3-indole boronic acids and tetrahydropyridine triflates

The palladium catalyzed cross-coupling reaction between 3-indole boronic acids and vinyl triflates is a good method to introduce vinyl groups into the indole 3-position. The regioselectivity of the enolization of N-substituted-3-piperidones is far greater than previously reported. N-tosyl-3-indole boronic acids can be easily synthesized via mercuration-boronation method.